Find Cheap Flights from Caribbean to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Caribbean to Chicago

(Round-trip)
Depart: Sat Jan 20 2018 Return: Tue Jan 30 2018 Trip spans 11 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
6h 57m
1 stop
Depart: Tue Feb 6 2018 Return: Mon Feb 19 2018 Trip spans 14 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
26h 03m
1 stop
Depart: Wed May 2 2018 Return: Sun May 6 2018 Trip spans 5 days
United
United
NAS
ORD
17h 05m
2 stops
ORD
NAS
3h 30m
nonstop
Depart: Tue Jan 23 2018 Return: Thu Jan 25 2018 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
6h 57m
1 stop
Depart: Tue Jan 30 2018 Return: Thu Feb 1 2018 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
6h 57m
1 stop
Depart: Wed Feb 14 2018 Return: Mon Feb 19 2018 Trip spans 6 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
26h 03m
1 stop
Depart: Sat Feb 3 2018 Return: Wed Feb 28 2018 Trip spans 26 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Tue Feb 6 2018 Return: Wed Feb 14 2018 Trip spans 9 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
6h 57m
1 stop
Depart: Thu Mar 1 2018 Return: Sun Mar 4 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 38m
1 stop
ORD
SJU
12h 28m
1 stop
Depart: Wed Feb 14 2018 Return: Wed Feb 21 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Wed Feb 21 2018 Return: Tue Feb 27 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 38m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Tue Jan 23 2018 Return: Fri Jan 26 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 14m
1 stop
ORD
SJU
15h 40m
3 stops
Depart: Wed Feb 21 2018 Return: Tue Feb 27 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 38m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Thu Dec 21 2017 Return: Thu Jan 4 2018 Trip spans 15 days
United
United
MBJ
ORD
4h 25m
nonstop
ORD
MBJ
7h 21m
1 stop
Depart: Mon Feb 26 2018 Return: Mon Mar 12 2018 Trip spans 14 days
Multiple Airlines
Multiple Airlines
BQN
ORD
9h 04m
1 stop
ORD
BQN
18h 12m
1 stop
Depart: Thu Feb 22 2018 Return: Wed Feb 28 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 38m
1 stop
ORD
SJU
6h 51m
1 stop
Depart: Tue Feb 27 2018 Return: Mon Mar 12 2018 Trip spans 13 days
Multiple Airlines
Multiple Airlines
BQN
ORD
9h 04m
1 stop
ORD
BQN
18h 12m
1 stop
Depart: Thu May 10 2018 Return: Sun May 13 2018 Trip spans 4 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 25m
1 stop
ORD
SJU
6h 49m
1 stop
Depart: Fri Jan 19 2018 Return: Mon Jan 22 2018 Trip spans 4 days
Multiple Airlines
Multiple Airlines
SJU
ORD
13h 51m
1 stop
ORD
SJU
6h 57m
1 stop
Depart: Wed Jan 10 2018 Return: Tue Jan 16 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 53m
1 stop
ORD
SJU
6h 57m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

Airports
Origin

Aguadilla
$272
Nassau
$306
San Juan
$188
Montego Bay
$343
Destination

Chicago
$188